US5227549A - Synthesis of 1,2-dichloroethane by ccl4 oxychlorination of ethylene - Google Patents

Synthesis of 1,2-dichloroethane by ccl4 oxychlorination of ethylene Download PDF

Info

Publication number: US5227549A
Authority: US; United States
Prior art keywords: sub; oxychlorination; ethylene; ccl; reaction
Prior art date: 1991-02-15
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

US07/835,868

Other languages

English (en)

Inventor

Yves Correia

Gerard Chastel

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Arkema France SA

Original Assignee

Elf Atochem SA

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1991-02-15

Filing date

1992-02-18

Publication date

1993-07-13

1992-02-18 Application filed by Elf Atochem SA filed Critical Elf Atochem SA

1992-03-25 Assigned to ELF ATOCHEM S.A. reassignment ELF ATOCHEM S.A. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: CHASTEL, GERARD, CORREIA, YVES

1993-07-13 Application granted granted Critical

1993-07-13 Publication of US5227549A publication Critical patent/US5227549A/en

2012-02-18 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims abstract description 22
239000005977 Ethylene Substances 0.000 title claims abstract description 22
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 title claims abstract description 10
230000015572 biosynthetic process Effects 0.000 title description 4
238000003786 synthesis reaction Methods 0.000 title description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims abstract description 62
238000006243 chemical reaction Methods 0.000 claims abstract description 25
239000003054 catalyst Substances 0.000 claims abstract description 22
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 15
239000001301 oxygen Substances 0.000 claims abstract description 15
229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
238000000034 method Methods 0.000 claims description 13
239000000203 mixture Substances 0.000 claims description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 2
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 abstract description 8
239000007789 gas Substances 0.000 abstract description 7
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 abstract description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
239000000460 chlorine Substances 0.000 description 14
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
229910052801 chlorine Inorganic materials 0.000 description 8
SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000000047 product Substances 0.000 description 7
239000000376 reactant Substances 0.000 description 7
229950011008 tetrachloroethylene Drugs 0.000 description 6
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 5
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 4
239000010949 copper Substances 0.000 description 4
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 4
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
229910052802 copper Inorganic materials 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
239000012530 fluid Substances 0.000 description 2
239000000395 magnesium oxide Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
QVLAWKAXOMEXPM-UHFFFAOYSA-N 1,1,1,2-tetrachloroethane Chemical class ClCC(Cl)(Cl)Cl QVLAWKAXOMEXPM-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000003570 air Substances 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical class ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 1
239000000017 hydrogel Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000004005 microsphere Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
150000002894 organic compounds Chemical group 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000002245 particle Substances 0.000 description 1
BNIXVQGCZULYKV-UHFFFAOYSA-N pentachloroethane Chemical compound ClC(Cl)C(Cl)(Cl)Cl BNIXVQGCZULYKV-UHFFFAOYSA-N 0.000 description 1
-1 perchloroethylene, trichloroethylene Chemical group 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000000197 pyrolysis Methods 0.000 description 1
238000004064 recycling Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/15—Preparation of halogenated hydrocarbons by replacement by halogens with oxygen as auxiliary reagent, e.g. oxychlorination
- C07C17/152—Preparation of halogenated hydrocarbons by replacement by halogens with oxygen as auxiliary reagent, e.g. oxychlorination of hydrocarbons
- C07C17/156—Preparation of halogenated hydrocarbons by replacement by halogens with oxygen as auxiliary reagent, e.g. oxychlorination of hydrocarbons of unsaturated hydrocarbons

Definitions

the present invention relates to the synthesis of 1,2-dichloroethane by oxychlorination of ethylene by means of carbon tetrachloride.
This oxychlorination reaction makes it possible to utilize the chlorine contained in the HCl.
French Patent No. 2,260,551 describes the oxychlorination of heavy chlorinated residues, namely, the reaction between these residues of ethylene and oxygen to produce perchloroethylene, trichloroethane, tetrachloroethane and D12.
South African Patent Application No. 71-5,781 published Mar. 27, 1972, describes a process for the oxychlorination of ethylene, to prepare a mixture of perchloroethylene and trichloroethylene.
the ethylene, the oxygen and the chlorine are passed over a fluidized bed catalyst based on copper chloride deposited onto a porous support, at a temperature ranging from 410° to 440° C.
the reaction is carried out in the presence of carbon tetrachloride originating from the recycling of the products exiting the fluidized bed.
the products exiting the fluidized bed are cooled to condense perchloroethylene, trichloroethylene and carbon tetrachloride.
the latter (CCl 4 ) is mixed with the feed gases (C 2 H 4 , Cl 2 and air) and is thus recycled to the fluidized bed.
the perchloroethylene and trichloroethylene constitute at least 50 mol % of the chlorinated products exiting the fluidized bed.
the amount of CCl 4 is constant and the CCl 4 does not accumulate. Its concentration does not exceed 10 mol % relative to the organic compounds charged into the fluidized bed, and this corresponds to a few percent relative to the total amount of the inlet gases.
the amount of chlorine, in the form of Cl 2 ranges from 40% to 75% of the chlorine-containing reactants introduced into the fluidized bed, about 2% to 8% is in the form of HCl and the remainder is organic chlorine-containing compounds (including CCl 4 ).
the atomic ratio of oxygen to carbon at the inlet to the fluidized bed ranges from 0.85 to 2. The overall result of this reaction, accordingly, is to produce perchloroethylene and trichloroethylene while consuming ethylene, chlorine (Cl 2 ) and oxygen.
a major object of the present invention is the provision of an improved process for the preparation of 1,2-dichloroethane (D12) and lesser amounts of its higher homologs, while consuming ethylene, CCl 4 and oxygen, according to the following reaction mechanism (2):
Another object of this invention is the provision of such improved oxychlorination process that utilizes the chlorine content of the CCl 4 .
CCl 4 is inevitably produced in too great an amount.
CCl 4 can itself be used as a source of chlorine in an ethylene oxychlorination reaction, namely, a mixture of CCl 4 , C 2 H 4 and O 2 (or air) can be passed over an oxychlorination catalyst to produce D12 and, in lesser amounts, its higher homologs such as trichloroethane and tetrachloroethane.
the present invention thus features a process for the synthesis of 1,2-dichloroethane, by contacting carbon tetrachloride, ethylene and oxygen with an oxychlorination catalyst at a temperature sufficient to form 1,2-dichloroethane, and thereafter separating said D12 from the products of reaction.
the subject reaction is carried out under normal conditions of oxychlorination in a fixed or fluid bed, over any catalyst based on alumina, silica magnesia or attapulgite and containing copper, but which may also contain the usual additives, potassium, magnesium and rare earths.
Suitable such catalysts are described, for example, in French Patents Nos. 1,555,518, 2,260,551, 2,063,365, 2,213,259 and 2,141,452, and European Patents Nos. 255,156, 257,561 and 176,432.
These catalysts generally comprise copper chloride deposited onto alumina of a specific surface area ranging from 50 to 450 m 2 /g and having a particle size ranging from 20 to 200 microns.
the amount of copper chloride, expressed as copper metal, advantageously ranges from 3% to 12% of the total weight of the catalyst.
catalysts comprising a mixture of the above catalysts and an inert material such as sand.
inert material such as sand.
the reaction temperature advantageously ranges from 220° to 450° C., in consideration that it is necessary to employ a temperature such that the conversion of the CCl 4 does not terminate at the Cl oxychlorinated derivative.
the pressure used advantageously ranges from atmospheric pressure to the usual upper limits for this type of process, namely, less than 10 bars.
the reaction is carried out in the presence of oxygen, most advantageously in the form of air.
hydrochloric acid with the starting materials.
the proportions of hydrochloric acid and carbon tetrachloride can vary widely, i.e., the reaction of the invention is between the two reaction schemes (1) and (2).
the feed of air (oxygen) and the feed of ethylene are adjusted to provide almost complete conversion of the ethylene and absence of HCl at the reaction zone outlet. This adjustment is known to the art of oxychlorination.
the proportion of CCl 4 and ethylene is such that the molar ratio CCl 4 /C 2 H 4 ranges from 0.4 to 1.6.
CCl 4 represents the sum of the number of moles of CCl 4 and one-quarter of the number of moles of HCl.
the proportion of oxygen and ethylene is such that the molar ratio O 2 /C 2 H 4 , the O 2 being expressed as air, ranges from 3 to 10. This indicates that a ratio of 5 signifies one mole of oxygen per mole of ethylene.
water vapor is added to the reaction mixture at the inlet to the catalyst bed, namely, the reaction mixture includes C 2 H 4 , O 2 (air), CCl 4 (optionally with HCl) and H 2 O.
the amount of water can vary widely and can range up to 2.5 moles per mole of CCl 4 at the inlet to the catalyst bed.
reaction products are recovered by means well known to the art of oxychlorination, for example cooling and condensing the less volatile products and separating them from the unreacted gases, followed by one or more distillations.
the residence times defined as the ratio of the volume of the catalyst (expanded, in the event of oxychlorination conducted in a fluid bed) to the feed rate of the reactants at the inlet to the bed at the reactor temperature are those typically employed in oxychlorination.
the height of the thus fluidized bed was 77 cm and the residence time was on the order of 12 seconds.
the gas exiting after condensation 31.27 Nliter contained 9.2% by volume of CO 2 and 12% by volume of oxygen. It was free of ethylene and was saturated with solvent at the temperature of 18° C.
the degree of conversion of the CCl 4 was 50% and that of the ethylene was 99.8%.
Example 2 The same reactor as described in Example 1 was used, but it was supplemented with measuring instruments typically employed industrially on-line in respect of the gases exiting oxychlorination reactors.
the reactants namely, air, hydrochloric acid, ethylene and carbon tetrachloride, were then introduced onto the same catalyst as described in Example 1.
the operating conditions, temperature, residence time and inlet flow rate of the reactants, as well as the flow rates of the excess reactants and of the products formed are reported in the Table below under the heading Example 2.
the degree of conversion of the CCl 4 was 47%, that of the ethylene was 99.8% and that of the oxygen was 79.7%.
Example 3 Using the apparatus described in Example 1, supplemented with the analytical instruments indicated in Example 2, two fresh experiments were carried out, of which the working conditions, entry flow rates of the reactants and exit flow rates of the excess reactants and of the products formed are reported in the following Table under the headings Example 3 and 4.

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

US07/835,868 1991-02-15 1992-02-18 Synthesis of 1,2-dichloroethane by ccl4 oxychlorination of ethylene Expired - Lifetime US5227549A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9101824A FR2672887B1 (fr)	1991-02-15	1991-02-15	Procede de synthese du 1,2-dichloroethane par oxychloration de l'ethylene au moyen du tetrachlorure de carbone.
FR91-01824		1991-02-15

Publications (1)

Publication Number	Publication Date
US5227549A true US5227549A (en)	1993-07-13

Family

ID=9409762

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
US07/835,868 Expired - Lifetime US5227549A (en)	1991-02-15	1992-02-18	Synthesis of 1,2-dichloroethane by ccl4 oxychlorination of ethylene

Country Status (14)

Country	Link
US (1)	US5227549A (fr)
EP (1)	EP0499512B1 (fr)
JP (1)	JPH0720892B2 (fr)
KR (1)	KR100203840B1 (fr)
CN (1)	CN1034166C (fr)
AT (1)	ATE101589T1 (fr)
CA (1)	CA2061100C (fr)
DE (1)	DE69200046T2 (fr)
DK (1)	DK0499512T3 (fr)
ES (1)	ES2062869T3 (fr)
FI (1)	FI101147B (fr)
FR (1)	FR2672887B1 (fr)
IE (1)	IE64742B1 (fr)
NO (1)	NO176910C (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6022188A (en) *	1996-10-28	2000-02-08	Siemens Westinghouse Power Corporation	Airfoil
US6680415B1 (en)	1999-11-22	2004-01-20	Dow Global Technologies Inc.	Oxyhalogenation process using catalyst having porous rare earth halide support
US20040152929A1 (en) *	2002-05-08	2004-08-05	Clarke William D	Process for vinyl chloride manufacture from ethane and ethylene with air feed and alternative hcl processing methods
US20040158110A1 (en) *	2001-05-23	2004-08-12	Schweizer Albert E.	Oxidative halogenation and optional dehydrogenation of c3+hydrocarbons
US6797845B1 (en)	1999-11-22	2004-09-28	Dow Global Technologies Inc.	Process for vinyl chloride manufacture from ethane and ethylene with immediate HCl recovery from reactor effluent
US6909024B1 (en)	1999-11-22	2005-06-21	The Dow Chemical Company	Process for the conversion of ethylene to vinyl chloride and novel catalyst compositions useful for such process
US6933417B1 (en)	1999-11-22	2005-08-23	Dow Global Technologies Inc.	Process for vinyl chloride manufacture from ethane and ethylene with partial CHl recovery from reactor effluent
US20070112233A1 (en) *	2005-11-17	2007-05-17	Lg Chem, Ltd.	Apparatus for preparing vinyl chloride by pyrolysis of 1,2-dichloroethane and method of preparing vinyl chloride using the same
DE102014223013A1 (de)	2014-11-12	2016-05-12	Volkswagen Aktiengesellschaft	Turbinenlaufrad, Turbine und Abgasturbolader

Citations (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1351700A (en) *	1970-09-28	1974-05-01	Fmc Corp	Production of chlorinated hydrocarbons
US3883605A (en) *	1967-05-19	1975-05-13	Pechiney Saint Gobain	Preparation of 1,2-dichloroethane and 1,1,2,2-tetrachloroethane by oxychlorination
US4754088A (en) *	1986-03-11	1988-06-28	Wacker-Chemie Gmbh	Process for oxychlorination of ethylene
US4849562A (en) *	1987-01-03	1989-07-18	The Dow Chemical Company	Process for producing ethylene dichloride

1991
- 1991-02-15 FR FR9101824A patent/FR2672887B1/fr not_active Expired - Fee Related
1992
- 1992-02-06 EP EP92400307A patent/EP0499512B1/fr not_active Expired - Lifetime
- 1992-02-06 ES ES92400307T patent/ES2062869T3/es not_active Expired - Lifetime
- 1992-02-06 DK DK92400307.2T patent/DK0499512T3/da active
- 1992-02-06 AT AT92400307T patent/ATE101589T1/de not_active IP Right Cessation
- 1992-02-06 DE DE69200046T patent/DE69200046T2/de not_active Expired - Fee Related
- 1992-02-11 IE IE920329A patent/IE64742B1/en not_active IP Right Cessation
- 1992-02-12 CA CA002061100A patent/CA2061100C/fr not_active Expired - Fee Related
- 1992-02-14 JP JP4059618A patent/JPH0720892B2/ja not_active Expired - Fee Related
- 1992-02-14 FI FI920655A patent/FI101147B/fi not_active IP Right Cessation
- 1992-02-14 NO NO920590A patent/NO176910C/no unknown
- 1992-02-15 KR KR1019920002278A patent/KR100203840B1/ko not_active Expired - Fee Related
- 1992-02-15 CN CN92100901A patent/CN1034166C/zh not_active Expired - Fee Related
- 1992-02-18 US US07/835,868 patent/US5227549A/en not_active Expired - Lifetime

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3883605A (en) *	1967-05-19	1975-05-13	Pechiney Saint Gobain	Preparation of 1,2-dichloroethane and 1,1,2,2-tetrachloroethane by oxychlorination
GB1351700A (en) *	1970-09-28	1974-05-01	Fmc Corp	Production of chlorinated hydrocarbons
US4754088A (en) *	1986-03-11	1988-06-28	Wacker-Chemie Gmbh	Process for oxychlorination of ethylene
US4849562A (en) *	1987-01-03	1989-07-18	The Dow Chemical Company	Process for producing ethylene dichloride

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6022188A (en) *	1996-10-28	2000-02-08	Siemens Westinghouse Power Corporation	Airfoil
US6933417B1 (en)	1999-11-22	2005-08-23	Dow Global Technologies Inc.	Process for vinyl chloride manufacture from ethane and ethylene with partial CHl recovery from reactor effluent
US20040097767A1 (en) *	1999-11-22	2004-05-20	Gulotty Robert J.	Oxyhalogenation process using catalyst having porous rare earth halide support
US6797845B1 (en)	1999-11-22	2004-09-28	Dow Global Technologies Inc.	Process for vinyl chloride manufacture from ethane and ethylene with immediate HCl recovery from reactor effluent
US6821924B2 (en)	1999-11-22	2004-11-23	Dow Global Technologies Inc.	Oxyhalogenation process using catalyst having porous rare earth halide support
US6909024B1 (en)	1999-11-22	2005-06-21	The Dow Chemical Company	Process for the conversion of ethylene to vinyl chloride and novel catalyst compositions useful for such process
US20050148805A1 (en) *	1999-11-22	2005-07-07	Jones Mark E.	Process for the conversion of ethylene to vinyl chloride, and novel catalyst compositions useful for such process
US6680415B1 (en)	1999-11-22	2004-01-20	Dow Global Technologies Inc.	Oxyhalogenation process using catalyst having porous rare earth halide support
US20040158110A1 (en) *	2001-05-23	2004-08-12	Schweizer Albert E.	Oxidative halogenation and optional dehydrogenation of c3+hydrocarbons
US6984763B2 (en)	2001-05-23	2006-01-10	Dow Global Technologies Inc.	Oxidative halogenation and optional dehydrogenation of c3+hydrocarbons
US20040152929A1 (en) *	2002-05-08	2004-08-05	Clarke William D	Process for vinyl chloride manufacture from ethane and ethylene with air feed and alternative hcl processing methods
US20070112233A1 (en) *	2005-11-17	2007-05-17	Lg Chem, Ltd.	Apparatus for preparing vinyl chloride by pyrolysis of 1,2-dichloroethane and method of preparing vinyl chloride using the same
DE102014223013A1 (de)	2014-11-12	2016-05-12	Volkswagen Aktiengesellschaft	Turbinenlaufrad, Turbine und Abgasturbolader
DE102014223013B4 (de) *	2014-11-12	2024-10-10	Volkswagen Aktiengesellschaft	Turbinenlaufrad, Turbine und Abgasturbolader

Also Published As

Publication number	Publication date
DE69200046D1 (de)	1994-03-24
FI920655A0 (fi)	1992-02-14
ES2062869T3 (es)	1994-12-16
IE64742B1 (en)	1995-09-06
KR920016393A (ko)	1992-09-24
NO920590D0 (no)	1992-02-14
NO176910C (no)	1995-06-21
DE69200046T2 (de)	1994-09-01
FI101147B (fi)	1998-04-30
CN1034166C (zh)	1997-03-05
JPH06279327A (ja)	1994-10-04
FR2672887B1 (fr)	1993-05-07
CA2061100C (fr)	2004-06-22
KR100203840B1 (ko)	1999-06-15
FR2672887A1 (fr)	1992-08-21
EP0499512A1 (fr)	1992-08-19
IE920329A1 (en)	1992-08-26
DK0499512T3 (da)	1994-07-18
FI920655L (fi)	1992-08-16
CN1067238A (zh)	1992-12-23
EP0499512B1 (fr)	1994-02-16
JPH0720892B2 (ja)	1995-03-08
NO920590L (no)	1992-08-17
NO176910B (no)	1995-03-13
ATE101589T1 (de)	1994-03-15
CA2061100A1 (fr)	1992-08-16

Legal Events

Date	Code	Title	Description
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